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Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols
Trifluoromethylated molecules have gained privileged recognition among the medicinal and pharmaceutical chemists. Sustainable photoredox- and electrochemical processes were employed to facilitate the relatively less explored radical cross-electrophile coupling to access trifluoromethyl- and allyl-su...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Elsevier
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8605352/ https://www.ncbi.nlm.nih.gov/pubmed/34841228 http://dx.doi.org/10.1016/j.isci.2021.103388 |
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author | Ashraf, Muhammad Awais Lee, Yunjeong Iqbal, Naila Iqbal, Naeem Cho, Eun Jin |
author_facet | Ashraf, Muhammad Awais Lee, Yunjeong Iqbal, Naila Iqbal, Naeem Cho, Eun Jin |
author_sort | Ashraf, Muhammad Awais |
collection | PubMed |
description | Trifluoromethylated molecules have gained privileged recognition among the medicinal and pharmaceutical chemists. Sustainable photoredox- and electrochemical processes were employed to facilitate the relatively less explored radical cross-electrophile coupling to access trifluoromethyl- and allyl-substituted tert-alcohols. Reactions proceed through trifluoromethyl ketyl radical and allyl radical intermediates, which undergo challenging radical-radical cross-coupling. The developed transformations are mild and chemo-selective to give cross-coupled products and deliver a wide range of valuable trifluoromethyl- and allyl-containing tertiary alcohols. Both processes can also be applied for the synthesis of amine variant containing trifluoromethyl and allyl moiety, which is considered as amide bioisostere. |
format | Online Article Text |
id | pubmed-8605352 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | Elsevier |
record_format | MEDLINE/PubMed |
spelling | pubmed-86053522021-11-26 Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols Ashraf, Muhammad Awais Lee, Yunjeong Iqbal, Naila Iqbal, Naeem Cho, Eun Jin iScience Article Trifluoromethylated molecules have gained privileged recognition among the medicinal and pharmaceutical chemists. Sustainable photoredox- and electrochemical processes were employed to facilitate the relatively less explored radical cross-electrophile coupling to access trifluoromethyl- and allyl-substituted tert-alcohols. Reactions proceed through trifluoromethyl ketyl radical and allyl radical intermediates, which undergo challenging radical-radical cross-coupling. The developed transformations are mild and chemo-selective to give cross-coupled products and deliver a wide range of valuable trifluoromethyl- and allyl-containing tertiary alcohols. Both processes can also be applied for the synthesis of amine variant containing trifluoromethyl and allyl moiety, which is considered as amide bioisostere. Elsevier 2021-10-30 /pmc/articles/PMC8605352/ /pubmed/34841228 http://dx.doi.org/10.1016/j.isci.2021.103388 Text en © 2021 The Author(s) https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Article Ashraf, Muhammad Awais Lee, Yunjeong Iqbal, Naila Iqbal, Naeem Cho, Eun Jin Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols |
title | Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols |
title_full | Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols |
title_fullStr | Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols |
title_full_unstemmed | Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols |
title_short | Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols |
title_sort | sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substituted tert-alcohols |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8605352/ https://www.ncbi.nlm.nih.gov/pubmed/34841228 http://dx.doi.org/10.1016/j.isci.2021.103388 |
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